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Ferrocene-Conjugated Oxidovanadium(IV) Complexes as Potent Near-IR Light Photocytotoxic Agents

Balaji, Babu and Banik, Bhabatosh and Sasmal, Pijus K and Maity, Basudev and Majumdar, Ritankar and Dighe, Rajan R and Chakravarty, Akhil R (2012) Ferrocene-Conjugated Oxidovanadium(IV) Complexes as Potent Near-IR Light Photocytotoxic Agents. In: European Journal of Inorganic Chemistry (1). pp. 126-135.

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejic.20...

Abstract

Ferrocene-conjugated oxidovanadium(IV) complexes [VO(Fc-tpy)(B)](ClO4)(2) (1-4) and [VO(Ph-tpy)(dppz)](ClO4)(2) (5) as a control [Fc = (eta(5)-C5H4)Fe-II(eta(5)-C5H5), Fc-tpy = 4'-ferrocenyl-2,2':6',2 `'-terpyridine, Ph-tpy = 4'-phenyl-2,2':6',2 `'-terpyridine, B = heterocyclic base: 2,2'-bipyridine (bpy in 1), 1,10-phenanthroline (phen in 2), dipyridoquinoxaline (dpq in 3), dipyridophenazine (dppz in 4)] were prepared and their DNA binding, DNA photocleavage activity and photocytotoxicity studied. The crystal structure of [VO(Fc-tpy)(bpy)](PF6)(2)center dot 3Me(2)CO shows a vanadyl group in six-coordinate (VON5)-O-IV coordination geometry, in which Fc-tpy and bpy display tridentate meridional and bidentate N-donor axial-equatorial binding modes, respectively. The one-electron paramagnetic complexes exhibit a charge-transfer band near 590 nm in DMF. The V-IV/V-III redox couple in 1-4 appears near -0.7 V, whereas the Fc moiety shows a response near 0.6 V vs. SCE in DMF/0.1 M TBAP. The complexes are good binders to calf thymus DNA with K-b values of 10(4)-10(6) M-1. DNA melting and viscometric data suggest groove and/or partial intercalative DNA binding of the complexes. Complexes 3-5 display DNA photocleavage activity in nearIR light of 785 nm. Complex 4 shows significant photocytotoxicity in visible light (400-700 nm) in HeLa cells with low dark toxicity.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to John Wiley and Sons.
Keywords: Medicinal chemistry;Ferrocene;Vanadium;DNA cleavage; Photodynamic therapy
Department/Centre: Division of Biological Sciences > Molecular Reproduction, Development & Genetics (formed by the merger of DBGL and CRBME)
Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 13 Apr 2012 09:06
Last Modified: 13 Apr 2012 09:06
URI: http://eprints.iisc.ernet.in/id/eprint/44276

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